
City Cast Chicago
❄️ Make the most of December in Chicago
December 1, 2025 · — Emmi Mack
Hey friends! Feeling well-rested? Bright-eyed and bushy-tailed? Good, because winter is beginning in Chicago. Fear not, though! City Cast Chicago has you covered with seasonal hacks, events to hit, and stories to watch. On today’s episode, we give you our guide to December 👇


What's CITY Talking About
Chicago School Board Rallies Behind Johnson's Budget Plan
City Council previously rejected Mayor Brandon Johnson’s $16.6 billion city budget, which would have allocated $552.4 million to Chicago Public Schools. Now, as the budget battle continues, Board of Education members and teachers are voicing support for Johnson’s vision, saying it would prevent cuts at CPS. [Chalkbeat]
- Meanwhile: CPS’ CEO search appears to stall. [Chalkbeat]
Where To Donate This Holiday Season
Thanksgiving is over, but the spirit of gratitude is strong in this city. As we gear up for Christmas, here’s a list of more than 60 local nonprofits and mutual aid groups where your dollars can help provide food, clothes, and more to Chicagoans in need. [Block Club]
- Related: How to help neighbors during ICE raids. [Hey Chicago 💻]

'Casino' Is Actually a Chicago Story
Martin Scorsese's classic “Casino” was inspired by the Chicago Outfit’s Las Vegas takeover during the ‘70s and ‘80s. The story was supposed to follow actual Chicago gangsters who oversaw Vegas operations … but studio lawyers put the kibosh on that. Here’s the real history. [Reader]
- That's okay: We have some great Chicago movies. [City Cast Chicago 🎧]
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Your Guide to Chicago in December 2025

Yes, it’s getting colder in Chicago. (As I write this, the wind is howling outside my window.) But December is jam-packed with so many events and spectacles, it’s not time to hunker down. Not yet.
Many (Many) Pop Ups
Pop-ups just feel like a party — whether it’s a bar or an artisan market. Lucky for us, December has plenty of both.
Some Holiday Pop-Up Experiences
- 🥂 Holly Jolly Christmas Bar | Puttery | West Loop
- 🥂 Gwen's Winter Curl & Chill | Gwen Hotel | Streeterville
- 🥂 Happy's Holiday Pop-Up Bar | Chicago Athletic Association | Loop
- 🥂 Rudolph's Bar | Lost Never Found | Wrigleyville
- 🥂 Santa Baby | Stolen Saddle | Wrigleyville
- 🥂 Château Carbide’s Winter Garden | Bar Pendry | Loop
- 🥂 Sweet Home Chicago | The Shops at North Bridge | Streeterville
- 🥂 Jack Frost Christmas Holiday Pop-Up | 170 N. Green St. | Fulton Market
Stay tuned in Hey Chicago for additional pop-up bars!
Upcoming Holiday Pop-Up Markets
- 🛍️ Holiday Party and Makers Market | Lillstreet Art Center | Ravenswood | Dec. 5
- 🛍️ Western Avenue Holiday Road + Trolley | Western Avenue between 99th to 115th Streets | Morgan Park and Beverly | Dec. 6
- 🛍️ Jarvis Square 17th Annual Artisan Market | Rogers Park | Dec. 6
- 🛍️ Drie-cember Market | Driehaus Museum | Streeterville | Dec. 6
- 🛍️ Puerto Rican Artisan Market | National Museum of Puerto Rican Arts and Culture | Dec. 6-7 and 12-13
- 🛍️ Gnarly or Nice – Holiday Ceramics Market | Co-Prosperity Sphere | Bridgeport | Dec. 13

Winter Fun in the Loop
Don’t be a Scrooge — get down to the Loop this season and take in the holiday merriment.
There’s ice skating every day (weather permitting) at Millennium Park and Maggie Daley Park, but reservations are required. Reserve for Millennium Park here and Maggie Daley here.
Personally, I prefer the ribbon at Maggie Daley, although Millennium Park is home to Chicago's official Christmas tree. See it twinkling in McCormick Tribune Plaza.
Nearby, at the Macy's on State Street, catch window displays paying tribute to Marshall Field’s. Upcoming reservations to the Marshall Field’s Walnut Room (recently renamed) are full, but you can reserve a slot at the store’s Santaland here.
And, of course, there’s always the Christkindlmarket at Daley Plaza, now in its 29th season. The open-air market ends on Dec. 24. Theaters downtown are also bustling with holiday options:
- 🎭 “The Christmas Carol” | Goodman Theatre | Runs through Dec. 31
- 🎭 “The Nutcracker” | Lyric Opera House | Runs through Dec. 28
- 🎭 “Twas the Night Before…” by Cirque du Soleil | Chicago Theatre | Runs through Dec. 28
"Dick Clark's New Year's Rockin' Eve" is also adding its first-ever Central time zone show this year, live from downtown. Hosts include Chance the Rapper and Ryan Seacrest ... will you be out there with them counting down?

What To Do
Monday, Dec. 1
- 🎼 Music of the Baroque | Symphony Center | Loop
- 🎥 A Day With(out) Art: "Meet Us Where We're At" | International Museum of Surgical Science | Streeterville
- 🎶 Of Monsters and Men | The Salt Shed | Goose Island
- 🎥 Kwaidan | Music Box Theatre | Southport Corridor
- 🕺🏻 Free Monday | Empty Bottle | Ukrainian Village
- 🤘 Punk Rock Monday | Delilah’s | Lincoln Park
- 📚 World Aids Day Panel: Raising Our Voices | Women & Children First | Andersonville
Tuesday, Dec. 2
- 🎶 Pentatonix: Christmas in the City Tour | Allstate Arena | Rosemont
- 🎭 "Elf The Musical" opens | The Auditorium | Loop
- 🎁 Holiday Gift Wrapping Station | South Chicago Branch
- 🧘 Meditative Yoga | Center on Halsted | Northalsted
- 📚 Get Lit: Santa's Book Fair | The American Writers Museum | Loop
- 🎶 The Arab Blues: Holiday Concert | Uptown Branch
- 👑 "SIX the Musical" opens | CIBC Theatre | Loop
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And now, I leave you with a poem: “Chicago and December” by W.S. Di Piero.
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